What disulfides would you obtain from oxidation of the following thiols? a. CH 3 CH 2 CH 2 SH b. 3-Methyl-1-butanethiol (skunk scent)

Hello, everyone. Today, we have the following problem predict the line structures of the disulfide products obtained from the oxidation of the thys listed below. So we have our first structure and our second line structure. So first, you want to draw our first structure out and to simplify this, we can essentially start by numbering the carbons from the right side that's closest to our sulfur group, such that we have 123, four and five. And we will not draw out the carbons in the parentheses just yet. So if we were to draw this, we have our carbons as such with our thy group at the end. And then remember we have 12345 carbons and so on carbon three, we have two methyl groups. So we will draw them as such. And now we just need to draw out the oxidation reaction. And essentially, we need to use two moles of this, this thy reactant. And so a shorthand notation is to simply remove the hydrogen from the Thile and they connect another sulfur and copy each part of the first structure such that we will have the following as our oxidation product. So we have our first sulfur group on the left and then on the right, we have our second one. So that takes care of our first structure. As for our second structure, we draw it out. We know that we have a thy group and that we have a Penta. That means we have a five carbon structure group. So if we were to half hour, five carbons, and if we count from right to left, such that the carbon bond to the sulfur gets the water priority, we will have 12345. And really quick, I will explain why we give the one to that carbon bond to the sulfur. And that is because the style group has the highest priority. So according to ie numbering or naming rules, we give the lowest priority to or we give the lowest number to the highest priority carbon. So we see that on carbon one, we have that pens th and then on carbon three, we have an ethyl group then as we did before, we will draw out the oxidation process and we will just remove the hydrogen and simply bond the other sulfur with a, an exact copy of the original structure. And so with that, we have solved the problem overall, I hope this helped. And until next time.

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14. Compounds with Oxygen or Sulfur

Reactions of Thiols

GOB Chemistry

14. Compounds with Oxygen or Sulfur

Reactions of Thiols

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Problem 17

Textbook Question

What disulfides would you obtain from oxidation of the following thiols?
a. CH₃CH₂CH₂SH
b. 3-Methyl-1-butanethiol (skunk scent)

Verified step by step guidance

Step 1: Understand the reaction. The oxidation of thiols (R-SH) leads to the formation of disulfides (R-S-S-R). This reaction involves the removal of hydrogen atoms from two thiol molecules and the formation of a covalent bond between the sulfur atoms.

Step 2: Write the general reaction for thiol oxidation. For a thiol molecule R-SH, the oxidation reaction can be represented as:

2 R - S H \to R - S - S - R + H_2

. This shows that two thiol molecules combine to form one disulfide molecule.

Step 3: Apply the reaction to part (a). For CH₃CH₂CH₂SH (1-propanethiol), two molecules of this thiol will react to form the disulfide. The product will be CH₃CH₂CH₂-S-S-CH₂CH₂CH₃ (1,1'-dithiobispropane).

Step 4: Apply the reaction to part (b). For 3-methyl-1-butanethiol, two molecules of this thiol will react to form the disulfide. The product will be 3-methyl-1-butanethiol disulfide, with the structure CH₃CH₂CH(CH₃)-S-S-CH(CH₃)CH₂CH₃.

Step 5: Verify the products. Ensure that the products are correctly named and that the sulfur atoms are bonded to each other in the disulfide linkage. The oxidation process does not alter the carbon backbone of the original thiol molecules.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Disulfide Formation

Disulfide formation occurs when two thiol groups (-SH) undergo oxidation, resulting in the creation of a covalent bond between the sulfur atoms, forming a disulfide bond (-S-S-). This reaction is crucial in biochemistry, as disulfides play a significant role in stabilizing protein structures.

Oxidation of Thiols

Oxidation of thiols involves the loss of electrons or hydrogen atoms from the thiol group, leading to the formation of disulfides. This process can be facilitated by various oxidizing agents and is essential in understanding the reactivity of thiols in organic chemistry.

Structural Isomers and Their Properties

Structural isomers, like 3-methyl-1-butanethiol, have the same molecular formula but different arrangements of atoms. Understanding the structural differences is important as they can influence the reactivity and properties of the thiols, affecting the types of disulfides formed during oxidation.

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